Vacation rentals with a patio in Sheboygan

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Top-rated patio rentals in Sheboygan

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Top guest favorite

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

Apartment in Sheboygan

4.97 out of 5 average rating, 157 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Guest favorite

An aerial view captures the stone castle set against expansive green fields and vineyards. A serene sunset casts warm light over the landscape, with the silhouette of the structure harmonizing with the rolling hills in the background.

Castle in Cleveland

4.99 out of 5 average rating, 143 reviews

Castle Vineyard –HOT TUB, Theater, Golf Sim, Sauna

As seen on the cover of Haven, a luxury home magazine! This masterpiece was built over the course of seven years and is officially open to the public in 2022! For travelers who want an exclusive taste of Tuscany without the hassle of jetting across an ocean, "The Castle Vineyard" is the place to stay. The dramatic, spellbinding stone castle proudly overlooks over twenty acres of idyllic rolling hills and a gorgeous, working vineyard. Once inside, the interior does nothing to dispel the magic.

Superhost

The fenced backyard displays a spacious green lawn, surrounded by wooden fencing. A patio area features a propane fire pit with several chairs arranged around it, inviting relaxation. Soft sunlight filters through nearby trees, creating a pleasant outdoor atmosphere.

Home in Sheboygan

4.83 out of 5 average rating, 247 reviews

Home Away From Home-One Block From Lake Michigan!

Centrally located and pet-friendly! Walk to the beach, parks, and downtown Sheboygan. This spacious two-story home perfect for groups features flexible bedroom setups, a fully equipped kitchen, dining room, fenced backyard, and parking for up to 4 vehicles. Base pricing is competitive for small groups $15/guest per night for more than 2 guests. Close to golf courses, many family spots, restaurants, and 16 miles from Road America. Watch “Sheboygan Airbnb” on YouTube for a full walkthrough!

Top guest favorite

A welcoming home exterior is shown with a well-maintained lawn and colorful flowerbeds. The facade features a combination of stone and siding, with large windows that allow ample natural light, and a covered entrance adds to the appeal.

Apartment in Port Washington

4.96 out of 5 average rating, 122 reviews

Picturesque Port Washington-HomePort LLC

The apartment is the lower level of our home in picturesque Port Washington. Quiet neighborhood, close to parks and close to bike path. There is 1 parking space and a separate entrance in the back of the house. There is a double futon in living area, bedroom has a queen size bed and newly renovated bathroom with a large shower. We are located 2 miles west of downtown Port which has many quaint shops, restaurants and a marina offering many opportunities for outdoor recreation and relaxation.

Guest favorite

A bright sunroom features tile flooring and large windows allowing natural light to fill the space. Several wooden chairs with striped cushions are arranged along the walls, accompanied by a small table draped in a white lace cloth. Decorative baskets are positioned overhead.

Home in Plymouth

4.92 out of 5 average rating, 103 reviews

Vintage Farmhouse on Blueberry Hill.

Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

Guest favorite

A red sports car is parked on a grassy area beside a two-story house, with large windows showcasing views of the lake. Surrounding trees provide a natural frame, while the glimmering water of the lake can be seen in the distance under a clear blue sky.

Home in Cleveland

4.93 out of 5 average rating, 15 reviews

New Listing: Private Lake Michigan beach home

Walk to your private beach without a bluff! Nestled between mature trees, Lakepines Cottage sits on 2 beautiful acres with over 200 feet of private beach. Offering breathtaking views of Lake Michigan, easy water access, flat lawn, walking trails through woods and prairies, and ample parking. This luxuriously appointed mid century modern home has everything you need just feet away from the beach. Lakepines Cottage is the perfect place to relax and make precious memories with your family.

Top guest favorite

An outdoor space is illuminated by soft lights against the night sky, featuring a cozy seating area with a firepit. Two green chairs are positioned around the fire, while a comfortable sectional sofa faces the warmth. Lush greenery and garden flowers enhance the tranquil atmosphere.

Home in Sheboygan

4.95 out of 5 average rating, 115 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Top guest favorite

Condo in Elkhart Lake

5 out of 5 average rating, 11 reviews

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

Top guest favorite

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

Apartment in Sheboygan

4.98 out of 5 average rating, 139 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

Top guest favorite

A serene sunset scene is displayed over the lake and river, with oranges and blues blending in the sky. Silhouetted trees and buildings frame the view, while the calm waters reflect the twilight colors. Streetlights line the road, illuminating the peaceful surroundings.

Home in Sheboygan

5 out of 5 average rating, 31 reviews

Unmatched Location, Views, & Style. Welcome Home!

Be in the heart of the all the action, The lake, river, marina, boardwalk, and downtown are mere steps from this newly constructed gem. The blue house on the hill is perched where the mouth of the Sheboygan River meets Lake Michigan. Take in the view mornings, evenings, and in between from the stunning kitchen, living room or sailboat shaped front porch. Entertain openly and relax at this one of a kind property. No stairs required. Ramp for easy age friendly access.

Guest favorite

The exterior of the house showcases a charming combination of brick and stucco with a classic gabled roof. Well-kept landscaping includes a small evergreen tree and planters at the entryway. A clear path leads to the front door, with bins placed beside the house.

Home in Kohler

4.97 out of 5 average rating, 29 reviews

The Kohler House

The Kohler House is located in the quaint village of Kohler. Our family grew up in this neighborhood and created a space to share with others that captures our love for the history and beauty that is Kohler. The home has been completely remodeled to blend a modern style with the historical architecture. It is our goal to not simply provide a space, but rather create a unique experience for our guests. We look forward to sharing our love of Kohler with you.

Guest favorite

A spacious beachfront condo is displayed, featuring a traditional style with white exterior and multiple balconies. Landscaping includes grass and trees, providing a green contrast to the building. Surrounding areas are visible, suggesting a well-maintained community environment.

Villa in Sheboygan

4.96 out of 5 average rating, 23 reviews

Perfect Paradise | 4BR Lakeview Condo w/ Jacuzzi

Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for families or groups. Enjoy a luxurious master suite with a 2-person jacuzzi tub, cozy gas fireplace, and private balcony overlooking the courtyard and Lake Michigan. With 7 beds, a fully stocked kitchen, in-unit washer/dryer, and stylish living spaces, comfort and convenience come standard. Your relaxing lakeside getaway starts here.